Oprah is an amazing woman. Interestingly, that is a statement that has been used to cliché throughout her 50-year career in the entertainment industry. It’s worth considering. Just how amazing is Oprah Winfrey? Well, she’s as influential as America’s First Lady. She is good friends with former First Lady Michelle Obama. The fact is, Oprah could easily be elected the first woman President of the United States.
She’s also an entertainment mogul who is worth $3 billion. And, Oprah single-handedly built her media empire from scratch. To accomplish this, she lifted herself out of abject poverty from deep in the heart of a racist Mississippi. Now lets take a look at her incredible life and an incredible house, she definitely worked very hard for it..
The Origins of a Media Queen
Oprah started as a news anchor for a local TV station. Next, she was hired to host a talk show in Chicago. She resurrected that talk show from an abysmal, last-place in ratings to first, making it the city’s highest-rated program. She flipped it practically overnight, and, eventually, it was hers. On that iconic talk show, she grew to be America’s spiritual leader and best friend. Whether it was picking the best diet plan, selecting choice monthly reads, or walking people away from grief to empathy, she was always there for viewers.
Her compassionate nature has been key to her success. It’s also indicative of her status as one of the nation’s most philanthropic people. To date, she’s donated $425 million to a variety of causes. She also never fails to fearlessly direct her media presence toward the good in this world, non-gratis, and oftentimes up against virulent backlash. So, where does America’s demigod live? What is it like being Oprah? Let’s find out!
Oprah’s Palatial Abode: A Prime Location
There are few places in Southern California more exclusive and tranquil than Montecito. Nestled just east of Santa Barbara and tucked into the Santa Ynez Mountains, the seaside town stretches from the live oak-dotted chaparral to the deep blues of the Pacific.
The Mediterranean climate of Montecito invites a community abundant in affluent properties, with trails for hiking and riding, weaving from the mountains to the sea. The median home price is over $3 million. With just an hour and a half drive to Los Angeles (even shorter by helicopter), it’s the perfect retreat. For Oprah and other celebs like Ellen DeGeneres and Jeff Bridges, who reside amongst its splendid beauty, it’s a natural wonder and a place they call home.
A Serendipitous Meeting
Just as hosting The Oprah Winfrey Show befell the world’s most successful woman by happenstance, so too, she discovered the Montecito property by random chance. Although truth be told, it is her immense talent as a performer and her incisive business acumen that made her show, and herself, a media sensation. In Steven Spielberg’s 1985 film, The Color Purple, she demonstrated her performance skills by earning an Oscar nomination for Best Supporting Actress. Separately, in a well-timed move, she was able to acquire ownership and production of The Oprah Winfrey Show from ABC. Additionally, she launched her own tremendously successful production company, Harpo Productions.
When she came across the Montecito mansion in 2001, she fell wildly in love with the property. As fate would have it, Oprah was looking for a place to call her own when she was invited to a party at the stunning Montecito estate. Wondrously captivated by the sprawling charm of the gorgeous beachfront property, she knew, then and there, it was destined to be hers. Clearly, she’s possessed of a dogged determination that invariably prevails.
She Made Them an Offer They Couldn't Refuse
At the time, Robert Veloz and his wife, Marlene, were living in the mansion’s newly remodeled 2,000-square-foot stone gatehouse. Veloz, president of The Veloz Group, an aeronautical equipment manufacturing giant, owned the property. He informed Oprah that neither the gatehouse nor the main house was up for sale.
Undeterred, she offered the couple $52 million. In total, the record sum was one of the nation’s largest private residence sales ever. Needless to say, Veloz relented allowing the media queen to establish her royal palace. After 25 years of hosting The Oprah Winfrey Show, the Montecito mansion was the perfect place to settle down. Undoubtedly, it was worth every penny.
Her Majesty’s Spread
The grounds that hold the sprawling property span 40 acres. Buffered by the hills on one end and the sea on the other, the vastness allows her more than a sense of privacy. Plus, views of the Santa Ynez range and the Channel Islands dotting the Pacific Ocean are spectacular. The mansion itself is a rambling 22,000 square feet. The opulent Georgian-style complex was constructed in 1912 but refurbished in 1959. With Oprah’s celebrity effect factored in, the property is currently worth over $100 million.
Inside the main house are eight bedrooms, fourteen bathrooms, and a pub. Naturally, it has two theaters and a gourmet kitchen among its array of rooms. It also features a wine cellar and ten fireplaces. Calling it home, at last, she found plenty of ways to enhance her fabulous abode.
Making it Feel Like Home
With the sale approved by Bob Veloz and his wife who purchased the property for $14 million in 1998, she was free to personalize the property. Wandering around the nine acres of immaculately landscaped grounds and beneath the natural sanctity of the canopy of native California live oaks while looking back at the plantation-style structure, Oprah felt the place needed a suitable identity, a term of endearment. Something that made it hers.
She loved the idea of owning her own plantation house and the symbolism it entailed. Based on Gone with the Wind, her first impulse sought to call it Tara II. But as she and her fitness guru Bob Greene meandered through the grounds, he felt another name could better capture the entirety. Tara, he opined, had nothing on this magnificent property. Since working on her film Beloved, she had been searching for a Southern plantation house—this one dwarfed those properties.
A Moment to Reflect Upon Abundant Grace
Bob Greene encouraged Oprah to fully celebrate the moment of her achievement. Not only was Oprah born in a small Mississippi town called Kosciusko where racist Jim Crow laws were heartily enforced, but she was also brought into the world under abysmal circumstances. Her mom, who was alone and only 15 when she was born, worked as a housemaid with no financial support from the father. Since her mother could not afford to care for her, she spent a lot of time with her grandmother who influenced her self-confidence and positive self-worth. Unfortunately, she was also destitute. Her first six years were spent in rural poverty with her grandmother who taught her to read at age three and took her to church.
Everyone was surprised by her proclivity to recite Bible verses. As a child, they called her “The Preacher.” Her grandmother dressed her in recycled potato sacks which prompted humiliating laughter from local children. There was plenty of struggle but look at what she attained! Bob suggested the name should be rooted in her past.
The Perfect Name for Oprah’s Palace
The Bible. That was it! Bob Greene hit upon the idea that the name of the estate should reflect her background in the Good Book and all she overcame to make it to this Southern California mecca. When he suggested “the Promised Land,” Oprah was immediately drawn to it. It resonated with her intense feelings of awe the palatial sanctuary engendered. And, using the Bible as her muse, the name seemed providential.
Now the fun part! Transforming her newly christened abode into her very own place, all 22,000 square feet of it. Remodeling and decorating would be one enormous undertaking, but also a very exciting project. She dove in with alacrity. The library came together beautifully. She calls it the “Reading Room” because that’s what she does there, duh. And It’s the perfect place to display her literary collection along with her book club picks. Being selected for Oprah’s book club generated a million additional book sales, whether or not the author is still living. John Steinbeck’s East of Eden hit the best seller’s list after Oprah’s Book Club read it.
Everyone’s Favorite Room: The Kitchen
When Oprah purchased the Promised Land, she loved the spacious, well-organized state-of-the-art kitchen arranged with a place for everything. But, for her, she decided it could be just a little bit more spacious. In order to accommodate her guests, who always tend to congregate in the most exciting area of the house, where the food and conversation is, she expanded.
Who prepares meals for the Queen O? The chef is certainly pampered here. The kitchen in the Montecito mansion came stocked with a fireplace, which is great for extra warmth (Southern California gets surprisingly chilly in the winter) and perfect for woodfired pizzas. But for Oprah, having a fireplace in the kitchen was just not as important as opening up everyone’s favorite room for more mingling space. So, she renovated the kitchen by removing the fireplace. She actually liked it, but the decision was made. You are welcome in the kitchen but please stay out of this next room!
Oprah’s Reading Room is Reserved for One Person
That person is her. Kindly stay out. Every book is carefully placed, organized and shelved, and she doesn’t want the order disturbed. Much like Oprah’s Book Club, it is thoughtfully planned. It contains her collections which she graciously allows guests to admire from a distance. It’s her sanctuary for reading, hence the name, the “Reading Room.” Decorated immaculately with artwork framed above wainscoted walls, a prettily placed doll is seated on the couch.
The doll is special. Not just because it is Oprah’s doll sitting on Oprah’s sofa, but because it reflects upon her childhood when, in sharp contrast, her house was cramped and rudimentary. Dolls were a luxury beyond her mother’s means. And even if dolls ended up in her hands, they wouldn’t be special like this one. This one is meticulously made with deep chocolate material which features a dark complexion, rather than being commonly constructed out of a creamy white fabric. Even though she was denied toys as a child, this one sits to attest.
A Room of One’s Own: The Exquisite Guest Room
Guests are gratefully directed away from the shelves of books in the Reading Room but are free to luxuriate in this sumptuous extravagance at their leisure. Warm and inviting with a pair of balcony windows, everything in this room exudes a delightful charm. Step outside to enjoy the view or settle down among the homey décor.
Pretty in pinks and lavenders, this room is soft and dainty and looks like a fabulous place to stay. It would be an honor, indeed, to be invited. With fresh-cut flowers adorning tables and a fireplace burning next to your choice of overstuffed chairs, it feels more like a luxurious B&B. And, yes, you must eventually leave. Each room has a unique style, let’s peek into this one.
Dinner at Oprah’s
Any masterpiece that comes out of that gourmet kitchen is going to look exquisite on this table. Polished to a gloss, the beautiful, extended dining table can accommodate plenty. Décor is subtle but elegant. Soft hues in the large area rug pull the room together. The chandelier candelabra is a delightful centerpiece to the room. Just imagine an evening with all the candelabras lit. Magnifique!
To remodel her home, Oprah auctioned off many items inside the Promised Land. She decided to redecorate so the Montecito mansion would better reflect her “true” self. The decision came after an L.A. designer bluntly told her, “This house has nothing to do with you.” Accordingly, Oprah bid farewell to her gilded mirrors and marble urns, among other items. All the proceeds were donated to her leadership academy for girls in South Africa. At the auction, someone paid $4,000 for her poster from Steven Spielberg’s The Color Purple.
The Story Behind the Tea House
This bright and airy room used to be a cutting room for the garden. When Oprah moved into the estate, she wanted that beautiful space for herself! Now it’s a tearoom. It’s also a sanctuary and a place to relax. Inside the tea house, you’ll find zero digital distractions. No music, no TV. It’s meant to be a secluded haven free from the hustle and bustle of the day. One is to be in the garden room with intention and peace.
Oprah goes there to read and meditate. It’s not a place for meetings, especially not business meetings. Never. It’s reserved for quiet reflection with a cup of tea. Even if months go by and she can seldom visit the tea house, just knowing it’s there is important to her. Having the tearoom is a dream come true. Going there is personally restorative for her. She values it, saying, “Alone time is when I distance myself from the voices of the world so I can hear my own.”
There’s More Than One Living Room in the Promised Land
Oprah’s mansion offers plenty of space for more than just one living room. This one, pictured here, is elegant yet comfy-cozy, warm and inviting yet chock full of breakable finery—keep the toddlers out! It’s a ground floor room with vaulted ceilings and a luxuriating spaciousness that can absorb a lot of furniture.
In this room, however, with two overstuffed couches and a large dining room-style table, it feels a little crowded. It’s also jam-packed with other pieces like ornate mirrors, lamps, side tables and pictures. It’s bursting with beauty! That’s exactly how Oprah felt. There was too much packed into one space. As a result, this room was also scheduled for redecorating. Oprah loves decorating. Engaging in home design is a passion of hers. The Promised Land is like her very own life-sized dollhouse. Enhancing her home and gardens as often as she likes is a wonderful pursuit. It’s a tremendous part of the affection she holds for the property.
Dripping in Wisteria: Views From the Tearoom
Another space Oprah adores to enhance is the garden. Stepping out of the tea house awaits a sumptuous treat. In the spring when the wisteria is in full bloom, sticky-sweet fragrant bunches of dainty lavender petals hang vine-like, clumped in clusters, over the trellis. These breathtaking blooms can be difficult to grow but, as pictured here, will dangle fantastically, like bunches of grapes, under the right conditions. It’s a treasured feature of the tearoom view.
Underneath the wisteria and down a few steps to a gravel path is a copper fountain surrounded by an English garden. Blooms of hydrangeas, lilies, dahlias, daffodils and other annuals and perennials delight. Beyond, is her formal rose garden. It’s extensive, boasting 600 rose bushes from a wide range of varieties. The gardens are an essential element of the wonder the Promised Land embodies. Oprah has compared the feeling of home that the Montecito mansion engenders to The Wizard of Oz. It’s that moment when Dorothy realizes she never had to look any further than her own backyard to be in the place that is most special to her. Sometimes, as she leaves the Promised Land, she is reminded of just how exceptional her home really is.
A Walk-in Closet Suited for a Queen
This glimpse into a section of Oprah’s closet looks like it could be an advert for a high-end clothing store. But no, it’s Oprah’s personal walk-in closet. The private sanctum is the most hallowed of the Promised Land’s halls. Tucked deep inside the complex, the sacred sepulcher may as well be as large as a women’s boutique shop, and it’s organized precisely. Fresh-cut flowers from the garden, no doubt, adorn the island shelving unit. She could spend hours in here!
Clothing is carefully placed inside sleek oak cabinetry. In exquisite fashion, each item is meticulously color-coded and organized on shelves, in cabinets, on hangers or in drawers. Nothing is out of place, especially the shoes! Like the centerpiece to the room, a stunning array of shoes crowns the space. Shelves, and shelves, and shelves of perfectly lined shoes, ordered by color and hue, it’s enough to arouse the green-eyed envy monster!
A Pretty Penny
In this photo, we get a peek inside the guest house. In this room, the work of David Simmons and Andrew Walker, Oprah’s designers, stands out. Particularly in the relief of Lincoln’s profile which is sculpted into an enormous one-cent piece and placed high above double doors. As if the room is beholden to the coppery plaque, accents in browns and bronzes predominate and are, in this way, set off prominently by wood in antique whitewash. To be sure, the piece holds a certain value.
There’s a story behind the pretty penny. It holds sentimental value. It was discovered by decorators Simmons and Walker, who are responsible for the majority of the interior decoration of the mansion. They found it at a vintage antique shop in Waukesha, Wisconsin. After Oprah turned six, she went to live with her mom in Milwaukee. The copper relief piece was found not far from the place Oprah grew up. The designers kept this find in mind. The garden is another place where designs are personalized for her majesty. Let’s go back out for a gander.
Behold, Hallelujah Lane: An Immaculate Garden Pathway
There are many aspects of the Promised Land that resonate with its name. Here, out in the garden down a cobblestone path, religious symbolism becomes more obvious. Hallelujah Lane, the pathway that leads into lush areas of the garden, finds dainty white climbing roses and more white hydrangea blooms that can be imagined. The sea of white hydrangeas was planted in homage to Oprah’s grandmother. Her grandmother would take her to church every Sunday. Hallelujah Lane preserves her grandmother’s memory in abundance.
When Oprah lived with her as a child, all they had was one white hydrangea bush in front of their front porch. Now she remembers the love of her grandmother with literally thousands of those beautiful plants. Amongst the blooms and down the biblical garden pathway is this beautiful addition to the garden, a white Greco-Roman statue which stands under wrought-iron arches and is surrounded by verdant beauty. Climbing over and through the wrought-iron arches are white-pink Sombreuil roses. Dense bushes of bright-white Iceberg roses encircle the statue.
Art in the Garden
Meandering through the garden finds many treasures. Here, in a grove of pine, eucalyptus and palm trees stand four bronze sculptures. The artist is Francisco Zúñiga, a Costa Rican-born man who lived in Mexico. He sculpted the bronze set in 1974. Zúñiga called the statue, “Grupo de Cuatro Mujeres de pie.” But how did this group of four women standing, as it is translated, find such a reverent place to stand?
It all started at Christie’s where Oprah discovered the fabulous piece. After winning the auction for $3.1 million, it was hers. The richness of its symbolism motivated her to invest the sizable sum. The set represents the stages of femininity. Each sculpture symbolizes one stage. Like an allegory of womanhood, the first portrays a teenage girl, the second, an expectant mother, the third, a middle-aged woman, and the fourth, an elderly woman. It adds another sense of cultivation to the outdoor grounds.
California Live Oaks Hold a Meaningful Place on the Promised Land
California live oaks are a hearty species that withstand fire, thrive with little precipitation, and grow strong as, well, strong as an oak. Oprah has a deep appreciation for her California natives, so much so that she has counted and named them. The twisting, sturdy branches of these natural wonders provide luxuriating shade. Oprah will often be found reading on a chaise under the shade of her favorite oak.
As it happened, there are twelve of these magnificent trees. In keeping with biblical themes, and in deference to their treasured place in her heart, Oprah named the grove of live oaks, the Twelve Apostles. She shares images of her magnificent disciples on Instagram. She also filmed her award-winning show Super Soul Sunday on the Oprah Winfrey Network (OWN) under these very trees. They give her a sense of peace. The Promised Land tends to do that.
Outdoors at the Promised Land has a lot to offer. From the fully manicured grounds to the areas where live oaks sprawl, it’s an ideal place for taking a walk or meditating. For Oprah, it’s a quiet retreat where she can be present and in tune with her inner peace. As the originator of the “aha moment,” she’s all about self-awareness. She also enjoys reading a book on the porch and drifting off with quiet daydreams. Her outdoor sanctuary is a place she goes for respite, and it’s just a step outside.
She has said that she enjoys being away from it all, even the TV. Sometimes she goes weeks without flipping it on. Once, she went an entire summer without television. It’s an escape that has become simpler after leaving The Oprah Winfrey Show behind.
Expanding the Wonderland
The Seamair equestrian farm, one of the largest properties in Montecito, borders the Promised Land. When Oprah moved in, she made sure to get to know her neighbors. Mary Dell Pritzlaff lived on Seamair Farms raising and training hackney ponies. The two became wonderful neighbors. After she died in 2001, the family of Mrs. Pritzlaff hoped the horse ranch would go to the Promised Land.
It did! Oprah’s property increased to a substantial 65 acres. That’s big enough to be her own private nature preserve! She was able to acquire the 23-acre farm by outbidding a developer. The price? She paid $28 million for the acreage which had not been on the market for 30 years. It includes the main house, a pool, an orchard, and a fish pond. Although it was fully-operational as an equestrian facility with stables, Winfrey chose not to keep the horses. Her plans for the acreage included planting a grove of mature oaks.
The Seamair Farms Ranch House
The main house at Seamair was designed by Cliff May in his signature, California Ranch-style architecture. He developed this characteristic style of architecture in the 1930s. After building thousands of these distinctive homes, his craft became popularly known as the California “dream home.” The post-War suburban homes are typified by sprawling, low-profile architecture. The Seamair dream home has five bedrooms, four baths, and spreads its living spaces across 5,000 square feet. And now it’s Oprah’s. Perhaps it will become a dream guest house?
The modern-style house sits on spectacular grounds. With 23 acres surrounding it, there is plenty of space for the equestrian equipment plus an orchard of fruit trees which includes an avocado grove. It also boasts of a fish pond teaming with Japanese koi and vibrant lily pads. The spacious orchards have been thriving for many years due to the previous owner’s exceptional knowledge in farming and gardening. But what will Oprah do with all that land? The purchase makes Oprah Montecito’s largest landowner.
The Stables Next Door
The extensive equestrian facility included a horse track and an expertly maintained riding course. There was plenty of room to take the Hackney ponies out for a brisk trot around the grounds in the privacy of their own backyard. It was a contented home, indeed, for those well-tended ponies.
The ranch house on the horse property is considerably smaller than Oprah’s mansion, about five times smaller, but it opens up possibilities to enhance the Promise Land. More significant is the land, and Oprah has been very interested in expanding her gardens into agriculture. There is also a greenhouse on the property that appeals to her love of horticulture. Most significant, it could be, is the fact that the Seamair property includes two existing wells. In Southern California, water is a premium, and Oprah loves to grow things. The landscaping on the Promise Land is extensive and she was briefly criticized by neighbors in Montecito for consuming too much water to keep up her grounds after she drilled a third well on the horse property. In fact, it was Jeff Bridges wife, Susan Geston, who made the public complaints. Montecito is definitely a celeb town!
California’s Perennial Water Problems
Oprah adores gardening. She enjoys the healthy living style that comes with reaping the bounty of her vegetable gardens. Fresh vegetables are plentifully available to her state-of-the-art kitchen, and she’s very proud of the work she puts into gardening. The only problem is, Southern California is technically a desert and drought issues never go away. During years following heavier rainfall, people celebrate the end of a drought, but, in general, it’s only a season away from another drought.
In California, when drought conditions exist, water use is regulated. Oprah had to cut her usage in half, as did other substantial water users. But, as the largest landowner in the area, when she drilled that third well on Seamair during moderate drought conditions, she heard about it. Drought is one problem, but when it rains, it pours.
California Wildfires and Mudslides Devastate Montecito
In December of 2017, Montecito was threatened by the Thomas Fire, the worst wildfire in California history. A month later, torrential rains doused the barren land. Stripped of the vegetation and roots that held the hillsides intact, catastrophic mudslides and floods (as native to California as earthquakes), inundated much of Montecito. Oprah’s home, too, fell victim to rivers of mud and floods.
At 3:47 a.m., she awoke to her dogs barking. It was pouring rain. Looking out the front window, a gas fire was blazing, and out the back, she couldn’t tell how deep the mud was. Concerned, she woke up her life partner, “her rock” of 30 years, Stedman Graham, and said, “Stedman, oh my god, something’s going on!” In the morning they surveyed the damage. The mud, pictured here, poured across her property. She shared a video of herself slogging through knee-high mud on Instagram. Fortunately, the damage the Promise Land sustained was minor compared with much of the community. Regardless, the natural disaster was extremely upsetting. Trapped there, while thirty miles of the legendary Highway 101 became a river of impassable mud, she reached out to a local friend for support.
Oprah and a Famous Friend FaceTime on TV
Sunday night she received a distinguished Golden Globe Award with a rousing speech about race and struggle and overcoming it all. The next morning, she woke up to the trial of mudslides. Distressed, she connected with another Montecito celeb and talked about their imperiled community. It was Ellen DeGeneres!
Ellen, completely distraught, talked about how she had been evacuated, along with much of Montecito, but equally, about how strong and supportive the community had been. “I love Montecito so much, it is the greatest community,” she said. She also got support from her good friend, Oprah. On a FaceTime call, Oprah, while coping with the mud, shared with The Ellen DeGeneres Show the extent of the damage. She talked about losing the back house and about being relatively spared. Meanwhile, Ellen told of the growing death toll, and she described the grim news of finding bodies in the mud. Oprah happened to have a team of Ventura County fire department search and rescue in her backyard. Reassured, she and Ellen thanked the crew live on Ellen’s daytime talk show via FaceTime.
Oprah Owns Other Exclusive Properties - Let’s Start in Telluride
Oprah is super-wealthy. Duh! But did you know, she is the highest-paid television personality, the richest self-made woman in the country, and the richest African American person of the entire 20th century? So, it’s no surprise she purchased the largest parcel of land in Telluride, Colorado, and then nabbed a high-tech luxury home on an adjacent lot. The purchase of the expansive 60-acre parcel set her back $11 million and the fabulous adjoining 3-plus acre property with the gorgeous house on it cost her about $14 million. She’s not worried.
Her place in the famous Telluride resort ski town is designed to withstand the winter wonderland. The driveway is wired to repel snow and set up to track and alert when cars pull up to the three-car garage. High-tech gadgetry runs the house, starting with the 1,600-bottle wine cellar. The five-bedroom, 6-bathroom home includes a fitness room (standard for Oprah) and a suspended fiber-optic bridge that connects the master bedroom to the office. Outdoors, an observation deck which cost $140,000 to build, is accessed by a walkway that sways in the treetops. Also installed, is a tram that cost $240,000. The deluxe convenience offers a one-minute tram ride to the slopes. Gotta have it.
Aloha! How Many Acres Does Oprah Own in Maui?
Oprah’s Maui mansion, snuggled into the hills near the lush rainforests of Hana, sets on an awesome 160 acres. However, she also owns an astounding 1,000 acres of Maui upcountry land near Mt. Haleakala which boasts a lavish 12-room B&B. When she comes to visit her palatial Hawaiian farmhouse, she arrives by private jet, naturally.
It wasn’t always so magnificent. When she purchased the property, the farmhouse needed a lot of work. The porch was small, the kitchen in disrepair and old-fashioned low ceilings impaired the view. She considered tearing it down. Bob Greene, her personal trainer and guru, who branched out to property management, advised against it. Instead, she hired an architect and a designer to restore the home. After stripping the house to its frame, the grey farmhouse was completely rebuilt into a dazzling white, exquisite 21-century farmhouse. Another dream home!
Oprah’s Pacific Northwest Property is Worth $8 Million
Oprah picked up this secluded Orcas Island compound located in Washington State for $8.275 million in 2018. Orcas Island, one of four islands that make up the San Juan Islands archipelago between Seattle and Vancouver, Canada, delights in unspoiled natural beauty. From her home, there is access to thousands of feet of west coast shoreline presenting serene sunset views. The secluded home, named Madroneagle Estate when it was built in 2007, luxuriates upon a 43-acre parcel.
Inside the home, 7,303 square feet are spread across four bedrooms and a guest house. Upstairs you’ll find a full-sized pool table and shuffleboard. Downstairs, a wine cellar with a tasting area is on hand. Outside is a woodworking studio, a gym, and a yoga studio. On the main floor, however, is the great place, the center of it all. It’s a soaring living room with an enormous area to chill, all highlighted by the crowning jewel, a kitchen that features a gigantic island and built-in pizza oven. There is plenty of room in this kitchen, just as Oprah likes it.
The Oprah Winfrey Show was filmed out of Chicago, Illinois. For 25 years, she appeared on the popular daily talk show. During those years she acquired quite a few Chicago digs.
She owned a duplex in Water Tower Place and a co-op in the Gold Coast building. But, gradually, she’s been getting rid of her properties in the area. Together, those two properties sold for $7.375 million. In 2018, she sold a 2,250-square-foot Colonial-style house in Elmwood Park. This was the last of her Chicago properties, it went for $375,000.
Time to Say Goodbye to Indiana and Florida, too
Oprah owned a 9,700-square-foot estate near Rolling Prairie, an area in northwestern Indiana. She had many fond memories there, but in 2003 she sold the Chicago retreat that included a large swimming pool and a 10-horse stable with riding areas for $8.5 million. She owned the 164-acre orchard and estate since 1988, just four years after she moved to Chicago to launch The Oprah Winfrey Show. Most people will recall that the program started out as a tabloid talk show.
In 2008 she got rid of her Fisher Island luxury condominium. Fisher Island, Florida is in an exclusive hub for celebs and wealthy elites. The plush waterfront two-bedroom home with spectacular ocean views was just under 2,000 square feet in size, but it listed it for a respectable $2 million.
One trait that distinguishes Oprah Winfrey is her philanthropic nature. From 2004 to 2010, she was ranked among the 50 most generous Americans. Not only that, but she is a role model of success and a natural leader for women and girls, a duty she heartily embraces. Throughout her career, Oprah donated a total of $425 million. Much of her giving focuses on education. She gave $100 million to the Oprah Winfrey Leadership Academy for Girls in South Africa where many girls at the academy are AIDS orphans. She also developed her own global charity organization called Oprah’s Angel Network. Winfrey went so far as to cover admin costs to make sure all donations would be put toward the cause. She’s a force to be reckoned with a tough act to follow!
Besides the Montecito mansion, the Maui “wowie” farmhouse, the Telluride spread, and the secluded Pacific Northwest rustic gem, she also owns a tropical vacation home on the Caribbean island of Antigua, a $7.75 million apartment in Chicago, and a $68 million home in New Jersey. Whew!